Dimethyl Sulfate → HCID 23023934, compound

HRID 1373854Notes

Reaction equation

HRID 1373854 reaction equation
[CH:1]1([C:7]2[CH:37]=[CH:36][C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[N:20]=[C:21]([NH:24][CH2:25][C:26]5[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=5)[S:22][CH:23]=4)=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(OC)(O[CH3:42])(=O)=O.[H-].[Na+].C(OC(C)C)(C)C>CN(C)C=O.O>[CH:1]1([C:7]2[CH:37]=[CH:36][C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[N:20]=[C:21]([N:24]([CH2:25][C:26]5[CH:27]=[CH:28][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:34][CH:35]=5)[CH3:42])[S:22][CH:23]=4)=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 23023998HCID 23023998, compound

Product 1

HCID 23023934HCID 23023934, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under an argon atmosphere, a suspension of methyl 4-(4-(4-(4-cyclohexylbenzyloxy)phenyl)-2-thiazolylaminomethyl)benzoate (65.0 g, 0.127 mol) obtained in Example 2(3) in N,N-dimethylformamide (130 ml) and dimethyl sulfate (15.0 ml, 0.159 mol) were successively added dropwise to a suspension of sodium hydride (content 60%, 6.09 g, 0.152 mol) in N,N-dimethylformamide (130 ml) at 10° C. or below and the mixture was stirred at room temperature for 1 hr. Diisopropyl ether (195 ml) and water (130 ml) were successively added dropwise at 10° C. or below, and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration, washed successively with diisopropyl ether (195 ml) and water (130 ml) and dried to give the title compound (56.0 g, 83.7%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed successively with diisopropyl ether (195 ml) and water (130 ml)
  4. customdried

Sources & evidence

ORD record
ord-86b0a3c1493f49a986225ddefeeb7b96
Source dataset
uspto-grants-2007_01
Patent number
US07163952B2

Reaction notes

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